1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent] → Methyl 3-fluoro-1H-indole-5-carboxylate

HRID 1976787Notes

Reaction equation

HRID 1976787 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[O-]S(C(F)(F)[F:19])(=O)=O.F[N+]1C(C)=CC(C)=CC=1C>CO>[CH3:13][O:12][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[C:3]2[F:19])=[O:11]

Participants

4

Reactant 2

HCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 53732549Methyl 3-fluoro-1H-indole-5-carboxylateYield 10.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-indole carboxylate (1.75 g, 10 mmol) and N-fluoro-2,4,6-trimethylpyridinium triflate (3.75 g, 13 mmol) in methanol (100 mL) was heated at reflux for 18 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel to provide 200 mg of the desired product.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-08eecb92640b4d11a217902a722df034
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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